An information processing apparatus including: a label acquisition section that acquires a label assigned by a user to a content selected among plural contents; a user certainty factor setting section that sets a user certainty factor to the label assigned by the user; a label prediction learning section that performs label prediction learning; a label prediction section that predicts a label regarding a content to which the label is not assigned, and calculates a label certainty factor that refers to certainty of the predicted label; a user certainty factor prediction section that performs user certainty factor prediction learning, and predicts a user certainty factor of (regarding) the predicted label of (regarding) the content to which the label is not assigned; and a selection section that selects a content to be next assigned a label among contents to which labels are not assigned.